(3aR,4aS,5S,5aR,6aR)-4a,5a-dimethyl-3-methylidene-5-(3-oxobutyl)-4,5,6,6a-tetrahydro-3aH-cyclopropa[f][1]benzofuran-2-one

Details

• Internal ID: c3f9805d-5ebc-4d99-a97f-746cf3ca7d37
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Xanthanolides
• IUPAC Name: (3aR,4aS,5S,5aR,6aR)-4a,5a-dimethyl-3-methylidene-5-(3-oxobutyl)-4,5,6,6a-tetrahydro-3aH-cyclopropa[f][1]benzofuran-2-one
• SMILES (Canonical): CC(=O)CCC1C2(C1(CC3C(C2)C(=C)C(=O)O3)C)C
• SMILES (Isomeric): CC(=O)CC[C@H]1[C@]2([C@@]1(C[C@@H]3[C@H](C2)C(=C)C(=O)O3)C)C
• InChI: InChI=1S/C16H22O3/c1-9(17)5-6-13-15(3)7-11-10(2)14(18)19-12(11)8-16(13,15)4/h11-13H,2,5-8H2,1,3-4H3/t11-,12-,13+,15+,16-/m1/s1
• InChI Key: UUCCDEBLQHHCHQ-XYTFPVCRSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.34 g/mol
• Exact Mass: 262.15689456 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• BDBM50433451

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.6712	67.12%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6186	61.86%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.9266	92.66%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8453	84.53%
P-glycoprotein inhibitior	-	0.7801	78.01%
P-glycoprotein substrate	-	0.8672	86.72%
CYP3A4 substrate	+	0.5260	52.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.6628	66.28%
CYP2C9 inhibition	-	0.8682	86.82%
CYP2C19 inhibition	-	0.7449	74.49%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	+	0.6393	63.93%
CYP2C8 inhibition	-	0.8482	84.82%
CYP inhibitory promiscuity	-	0.8315	83.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6215	62.15%
Eye corrosion	-	0.9846	98.46%
Eye irritation	-	0.7832	78.32%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8915	89.15%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5572	55.72%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.5766	57.66%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6960	69.60%
Acute Oral Toxicity (c)	III	0.5894	58.94%
Estrogen receptor binding	+	0.5815	58.15%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5597	55.97%
Glucocorticoid receptor binding	+	0.7111	71.11%
Aromatase binding	-	0.6234	62.34%
PPAR gamma	-	0.6521	65.21%
Honey bee toxicity	-	0.8666	86.66%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9964	99.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.26%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.18%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.86%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.29%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.09%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.67%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.31%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.29%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	81.16%	90.17%

Plants that contains it

• Arnica longifolia
• Capsicum annuum
• Carpesium abrotanoides
• Carpesium faberi
• Lilium pumilum

Cross-Links

• PubChem: 53319263
• NPASS: NPC219011
• ChEMBL: CHEMBL1644102
• LOTUS: LTS0237851
• wikiData: Q105279235